What kind of hairstyle/haircut would go on him?

Assuming there are no issue with having the ears free of hair, a good barber should be able to design a regular haircut or one of the short pomp(pompadour) styles-crew cut, ivy league(long crew cut), flat top crew cut- to fully suit as is true for most young guys. Most girls are fine with whatever standard medium to short style a guy chooses to wear as long as the style fully suits and is kept clean and looking well groomed and the guy doesn't spend a lot of time on his hair. If a guy wants to go to a shorter style for the summer or one of his sporting activities, that is fine with most girls too even when she prefers that he wear a somewhat longer style. Longer styles where the hair covers the ears and collar are also possible but best doe by a stylist good with guy's haircuts. Hair grows at an average rate of 1/8" per week. A photo is the best way to describe a style to a barber or stylist.

regular haircut:

http://www.gstatic.com/hostedimg/55c5c155a74bf22b_...

ttp://oi54.tinypic.com/1445gn5.jpg

ivy league(long crew cut):

worn spiked up....

http://www.gstatic.com/hostedimg/45368d8c59451f3a_...

ttp://oi50.tinypic.com/1fdywx.jpg

ttp://oi46.tinypic.com/sgpjs7.jpg

worn down and brushed to the side...

http://www.gstatic.com/hostedimg/d2e97250e0614ff6_...

medium crew cut:

http://books.google.com/books?id=x0EEAAAAMBAJ&lpg=...

http://books.google.com/books?id=TT3U8oTBjRAC&lpg=...

ttp://www.gstatic.com/hostedimg/

ae218215599f9a96_large

ttp://oi48.tinypic.com/2i209b6.jpg

ttp://oi49.tinypic.com/iqzl80.jpg

short crew cut:

http://www.gstatic.com/hostedimg/dfbf10e504bce8a1_...

Some barbers consider that all crew cuts should have a flat top, so it is best to not rely on words alone for even a widely recognized style like a crew cut.

flat top crew cut:

http://books.google.com/books?id=Tyzj1RDXy8kC&lpg=...

ttp://oi48.tinypic.com/f0dumb.jpg

ttp://oi50.tinypic.com/2ymzhq8.jpg

ttp://oi48.tinypic.com/k4b29f.jpg

ttp://oi50.tinypic.com/2v33tok.jpg

regular haircut to summer crew cut:

http://books.google.com/books?id=gEwEAAAAMBAJ&lpg=...

Pg 27, two sixteen year old guys with crew cuts; pg 26, same guys with regular haircuts:

http://books.google.com/books?id=Xg6dEKlEnr4C&lpg=...

Search the internet for images of football(soccer)star Lukas Podolski for examples of ivy league and crew cut styles. A minute dab of control wax aka butch wax will keep the hair looking well groomed at crew cut and ivy league length. A butch comb also helps with grooming the short pomp styles- the small, flat, plastic, oval, pocket brushes that one finger fits through and barbers sell for about a dollar. A boar bristle military brush is usually available for a few dollars and while too large for a guy to carry in his pocket, is nice to have at home.

ttp://oi55.tinypic.com/xf83tc.jpg

here are a few regular haircuts:

ttp://oi60.tinypic.com/ivvorn.jpg

ttp://oi59.tinypic.com/10pxb7p.jpg

ttp://oi61.tinypic.com/t558cl.jpg

ttp://oi62.tinypic.com/206kg2h.jpg

Same guy as above, hair groomed with a little dab of brylcreem...

ttp://oi60.tinypic.com/uo603.jpg

An ivy league, is considered to be a convertible haircut as it can be styled several ways...

1) Lightly waxed, side parted and brushed to the side with a short pompadour at the front hairline.

2)) Lightly waxed, side parted and brushed to the side without a short pompadour at the front hairline.

3) Lightly waxed and brushed back off the forehead like a crew cut.

4) Lightly waxed with the top hair brushed forward and the short bangs on the forehead like a forward brush.

5) Lightly waxed with the top hair brushed forward and the short bangs brushed back off the forehead like a crew cut.

here are more than a few ivy leagues...

ttp://oi43.tinypic.com/15nnb06.jpg

ttp://oi41.tinypic.com/ohu73a.jpg

ttp://oi39.tinypic.com/28hq5nq.jpg

ttp://oi41.tinypic.com/1ktcl.jpg

ttp://oi42.tinypic.com/15f6kif.jpg

ttp://oi42.tinypic.com/ftncdk.jpg

ttp://oi41.tinypic.com/15pq0w0.jpg

ttp://oi40.tinypic.com/rcvfcx.jpg

ttp://oi39.tinypic.com/155iejo.jpg

ttp://oi42.tinypic.com/rarptx.jpg

ttp://oi44.tinypic.com/zvrgac.jpg

ttp://oi39.tinypic.com/o06yao.jpg

ttp://oi43.tinypic.com/2a6pog6.jpg

ttp://oi39.tinypic.com/2hd2lbl.jpg

ttp://oi41.tinypic.com/dqiq0z.jpg

The flat top crew cut is practically not seen at all on young guys at the moment but has usually been the most popular short style. In the 50's and 60's at least the first half till the beatles influence made short styles almost anathema, it was the most popular short style and then from the mid 80s to around 2000, was practically the only short style worn by young guys.

A few flats....

ttp://oi60.tinypic.com/2ibdggi.jpg

ttp://oi59.tinypic.com/104k9ib.jpg

ttp://oi57.tinypic.com/55mjav.jpg

ttp://oi59.tinypic.com/15ewu1i.jpg

ttp://oi60.tinypic.com/2n7dvub.jpg

ttp://oi59.tinypic.com/16kqhle.jpg

ttp://oi62.tinypic.com/23itj4z.jpg

ttp://oi61.tinypic.com/m9yvbm.jpg

a few more....

ttp://oi58.tinypic.com/2j19942.jpg

ttp://oi59.tinypic.com/fmoutg.jpg

ttp://oi62.tinypic.com/289lq1s.jpg

ttp://oi62.tinypic.com/2gws6td.jpg

ttp://oi62.tinypic.com/1072jd5.jpg

ttp://oi57.tinypic.com/4pypsw.jpg

ttp://oi61.tinypic.com/53kabm.jpg

same west point cadet, standard prep uniform...

ttp://oi62.tinypic.com/htwj12.jpg

ttp://oi60.tinypic.com/5u4hau.jpg

ttp://oi58.tinypic.com/dwxw20.jpg

Flats and Crews...

ttp://oi39.tinypic.com/2vafpsn.jpg

ttp://farm8.staticflickr.com/

7123/7881261778_8155883af4_o.jpg

ttp://oi39.tinypic.com/nujie.jpg

ttp://oi44.tinypic.com/5b348y.jpg

ttp://oi39.tinypic.com/2wf1xrq.jpg

ttp://oi41.tinypic.com/29p2hqo.jpg

ttp://oi44.tinypic.com/ip169y.jpg

ttp://oi58.tinypic.com/21o1t2c.jpg

ttp://oi60.tinypic.com/f8dvd.jpg

ttp://oi59.tinypic.com/1zdsldi.jpg

Shave the fro man. Go buzz cut

buzz cut